PL105054B1 - Sposob wytwarzania estrow kwasu 7-acyloamido-3-metylo-3-cefemokarboksylowego-4 - Google Patents

Sposob wytwarzania estrow kwasu 7-acyloamido-3-metylo-3-cefemokarboksylowego-4 Download PDF

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Publication number: PL105054B1
Authority: PL; Poland
Prior art keywords: acid; ester; sulfoxide; group; methyl
Prior art date: 1974-12-13

Application number

PL1975185465A

Other languages

English (en)

Polish (pl)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-12-13

Filing date

1975-12-12

Publication date

1979-09-29

1975-12-12 Application filed filed Critical

1979-09-29 Publication of PL105054B1 publication Critical patent/PL105054B1/pl

Links

238000000034 method Methods 0.000 title claims description 49
239000002253 acid Substances 0.000 title claims description 43
150000002148 esters Chemical class 0.000 title description 30
238000004519 manufacturing process Methods 0.000 title description 12
-1 penicillanic acid sulfoxide ester Chemical class 0.000 claims description 45
230000008569 process Effects 0.000 claims description 27
239000002904 solvent Substances 0.000 claims description 22
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 14
150000003462 sulfoxides Chemical class 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
238000010438 heat treatment Methods 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
XJMFIMBSWLGRQW-UHFFFAOYSA-N P(O)(O)=O.ClCCl Chemical class P(O)(O)=O.ClCCl XJMFIMBSWLGRQW-UHFFFAOYSA-N 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 2
UMHSKYSHOIGDPE-UHFFFAOYSA-N pyridine;quinoline Chemical compound C1=CC=NC=C1.N1=CC=CC2=CC=CC=C21 UMHSKYSHOIGDPE-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
229930182555 Penicillin Natural products 0.000 description 20
230000008707 rearrangement Effects 0.000 description 18
229940049954 penicillin Drugs 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229930186147 Cephalosporin Natural products 0.000 description 11
125000003277 amino group Chemical group 0.000 description 11
229940124587 cephalosporin Drugs 0.000 description 11
230000003115 biocidal effect Effects 0.000 description 10
238000009835 boiling Methods 0.000 description 10
125000004185 ester group Chemical group 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 7
229940106164 cephalexin Drugs 0.000 description 7
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 description 6
ZYDCYYCORHLHDQ-UHFFFAOYSA-N P([O-])([O-])=O.ClCCl.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1 Chemical compound P([O-])([O-])=O.ClCCl.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1 ZYDCYYCORHLHDQ-UHFFFAOYSA-N 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
150000001780 cephalosporins Chemical class 0.000 description 6
239000000203 mixture Substances 0.000 description 6
150000002960 penicillins Chemical class 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
238000006049 ring expansion reaction Methods 0.000 description 5
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
230000009471 action Effects 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
235000007708 morin Nutrition 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
MFEIKQPHQINPRI-UHFFFAOYSA-N 3-Ethylpyridine Chemical compound CCC1=CC=CN=C1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
AILGYMJQGYXXIK-BDPMCISCSA-N (4-nitrophenyl)methyl (6r)-3-methyl-8-oxo-7-(phenoxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)COC1=CC=CC=C1 AILGYMJQGYXXIK-BDPMCISCSA-N 0.000 description 1
KZVOLMLGLGADDW-NQPNHJOESA-N (6R)-7-amino-3-methyl-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound CC1=CN2[C@H](SC1)C(N)C2=O KZVOLMLGLGADDW-NQPNHJOESA-N 0.000 description 1
LFMBIMXJWIQULB-SSDOTTSWSA-N (6r)-3-methyl-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC(C)=CN2C(=O)C[C@H]21 LFMBIMXJWIQULB-SSDOTTSWSA-N 0.000 description 1
NQNQSDYQPRGBSF-YOXFSPIKSA-N (6r)-4-acetamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(C)C(NC(=O)C)S[C@@H]2CC(=O)N21 NQNQSDYQPRGBSF-YOXFSPIKSA-N 0.000 description 1
VZKHCRJSGAACIM-KGMSYRRLSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid Chemical compound S1C(C(O)=O)C(C)=CN2C(=O)C(N)[C@@H]12 VZKHCRJSGAACIM-KGMSYRRLSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
WKFYEWXSRFQOKX-UHFFFAOYSA-N 1,4-dioxane;toluene Chemical compound C1COCCO1.CC1=CC=CC=C1 WKFYEWXSRFQOKX-UHFFFAOYSA-N 0.000 description 1
PBYMYAJONQZORL-UHFFFAOYSA-N 1-methylisoquinoline Chemical class C1=CC=C2C(C)=NC=CC2=C1 PBYMYAJONQZORL-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XOUWYLIJSZZUDB-UHFFFAOYSA-N ClC1=CC=CC=[N+]1Cl Chemical compound ClC1=CC=CC=[N+]1Cl XOUWYLIJSZZUDB-UHFFFAOYSA-N 0.000 description 1
241001428016 Glaucosciadium clade Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
101000901617 Notophthalmus viridescens Homeobox protein DLX-3 Proteins 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000003990 capacitor Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
238000007257 deesterification reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
IXTGXVWLIBNABC-UHFFFAOYSA-N dichloromethylphosphonic acid Chemical compound OP(O)(=O)C(Cl)Cl IXTGXVWLIBNABC-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003292 glue Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005179 haloacetyl group Chemical group 0.000 description 1
230000004217 heart function Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
239000011435 rock Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003860 tertiary carboxamides Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Cephalosporin Compounds (AREA)

PL1975185465A 1974-12-13 1975-12-12 Sposob wytwarzania estrow kwasu 7-acyloamido-3-metylo-3-cefemokarboksylowego-4 PL105054B1 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/532,536 US3953440A (en)	1974-12-13	1974-12-13	Deacetoxycephalosporins via penicillin sulfoxide rearrangement

Publications (1)

Publication Number	Publication Date
PL105054B1 true PL105054B1 (pl)	1979-09-29

Family

ID=24122205

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1975185465A PL105054B1 (pl)	1974-12-13	1975-12-12	Sposob wytwarzania estrow kwasu 7-acyloamido-3-metylo-3-cefemokarboksylowego-4

Country Status (26)

Country	Link
US (1)	US3953440A (nl)
JP (1)	JPS5532715B2 (nl)
AR (1)	AR208576A1 (nl)
AT (1)	AT344893B (nl)
BE (1)	BE836414A (nl)
BG (1)	BG26393A3 (nl)
CA (1)	CA1053225A (nl)
CH (1)	CH601308A5 (nl)
CS (1)	CS203983B2 (nl)
DD (1)	DD123753A5 (nl)
DE (1)	DE2555183C3 (nl)
DK (1)	DK141502B (nl)
ES (1)	ES443462A1 (nl)
FR (1)	FR2294178A1 (nl)
GB (1)	GB1535341A (nl)
GR (1)	GR59923B (nl)
HU (1)	HU173324B (nl)
IE (1)	IE42380B1 (nl)
IL (1)	IL48602A (nl)
NL (1)	NL175623C (nl)
PH (1)	PH13532A (nl)
PL (1)	PL105054B1 (nl)
RO (1)	RO68208A (nl)
SE (1)	SE426829B (nl)
YU (1)	YU304675A (nl)
ZA (1)	ZA757743B (nl)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1465893A (en) *	1973-02-09	1977-03-02	Gist Brocades Nv	I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use
ES431585A1 (es) *	1974-11-02	1976-11-16	Gema Sa	Procedimiento para la transformacion de acido 6-aminopeni- cilanico en 7-amino-desacetoxicefalosporanico.
US20060201522A1 (en) *	2005-03-10	2006-09-14	Yoshiaki Sato	Method for lowering blood glucose levels, method of treating diabetes, and method of prevention of diabetes
CN102432627A (zh) *	2011-09-19	2012-05-02	江苏九九久科技股份有限公司	生产对硝基苄基青霉素g亚砜酯的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3819622A (en) *	1969-03-11	1974-06-25	Glaxo Lab Ltd	Method of producing 7beta-acylamido-3-methylceph-3-em-4-carboxylic acid esters
HU167757B (nl) *	1969-03-11	1975-12-25
GB1312233A (en) *	1969-12-05	1973-04-04	Glaxo Lab Ltd	Cephalosporin compounds
US3843637A (en) *	1971-05-11	1974-10-22	Bristol Myers Co	Process for rearranging 6-acylamidopenicillanic acid-1-oxides to 7-acyla mido-3-methyl-ceph-3-em-4-carboxylic acids
JPS4844296A (nl) *	1971-10-14	1973-06-26
NL7303263A (nl) *	1972-03-09	1973-09-11
JPS536158B2 (nl) *	1972-03-23	1978-03-04
JPS4943999A (nl) *	1972-09-01	1974-04-25

1974
- 1974-12-13 US US05/532,536 patent/US3953440A/en not_active Expired - Lifetime
1975
- 1975-12-03 CA CA241,008A patent/CA1053225A/en not_active Expired
- 1975-12-03 YU YU03046/75A patent/YU304675A/xx unknown
- 1975-12-03 IL IL48602A patent/IL48602A/xx unknown
- 1975-12-03 GR GR49523A patent/GR59923B/el unknown
- 1975-12-04 SE SE7513702A patent/SE426829B/xx not_active IP Right Cessation
- 1975-12-05 PH PH17835A patent/PH13532A/en unknown
- 1975-12-05 AR AR261513A patent/AR208576A1/es active
- 1975-12-08 NL NLAANVRAGE7514296,A patent/NL175623C/nl not_active IP Right Cessation
- 1975-12-08 DE DE2555183A patent/DE2555183C3/de not_active Expired
- 1975-12-09 GB GB50354/75A patent/GB1535341A/en not_active Expired
- 1975-12-09 JP JP14681975A patent/JPS5532715B2/ja not_active Expired
- 1975-12-09 DK DK556475AA patent/DK141502B/da not_active IP Right Cessation
- 1975-12-09 BE BE1007067A patent/BE836414A/xx not_active IP Right Cessation
- 1975-12-10 RO RO7584155A patent/RO68208A/ro unknown
- 1975-12-10 ZA ZA757743A patent/ZA757743B/xx unknown
- 1975-12-10 FR FR7537770A patent/FR2294178A1/fr active Granted
- 1975-12-11 HU HU75EI659A patent/HU173324B/hu unknown
- 1975-12-11 BG BG7531760A patent/BG26393A3/xx unknown
- 1975-12-11 IE IE2703/75A patent/IE42380B1/en unknown
- 1975-12-11 AT AT940875A patent/AT344893B/de not_active IP Right Cessation
- 1975-12-12 CS CS758486A patent/CS203983B2/cs unknown
- 1975-12-12 DD DD190104A patent/DD123753A5/xx unknown
- 1975-12-12 PL PL1975185465A patent/PL105054B1/pl unknown
- 1975-12-12 CH CH1616375A patent/CH601308A5/xx not_active IP Right Cessation
- 1975-12-12 ES ES443462A patent/ES443462A1/es not_active Expired

Also Published As

Publication number	Publication date
FR2294178A1 (fr)	1976-07-09
JPS5532715B2 (nl)	1980-08-26
FR2294178B1 (nl)	1979-10-19
NL7514296A (nl)	1976-06-15
AU8730175A (en)	1977-06-09
DK141502C (nl)	1980-09-22
IL48602A (en)	1979-03-12
NL175623B (nl)	1984-07-02
IL48602A0 (en)	1976-02-29
DE2555183C3 (de)	1981-10-29
HU173324B (hu)	1979-04-28
AR208576A1 (es)	1977-02-15
SE7513702L (sv)	1976-06-14
AT344893B (de)	1978-08-10
CS203983B2 (en)	1981-03-31
IE42380B1 (en)	1980-07-30
NL175623C (nl)	1984-12-03
BE836414A (fr)	1976-06-09
DE2555183B2 (de)	1980-09-11
DK556475A (nl)	1976-06-14
DE2555183A1 (de)	1976-06-16
DK141502B (da)	1980-03-31
GR59923B (en)	1978-03-20
SE426829B (sv)	1983-02-14
PH13532A (en)	1980-06-19
DD123753A5 (nl)	1977-01-12
BG26393A3 (nl)	1979-03-15
CA1053225A (en)	1979-04-24
ZA757743B (en)	1977-07-27
ATA940875A (de)	1977-12-15
GB1535341A (en)	1978-12-13
JPS5182293A (nl)	1976-07-19
RO68208A (ro)	1980-08-15
CH601308A5 (nl)	1978-07-14
YU304675A (en)	1982-05-31
ES443462A1 (es)	1977-08-16
IE42380L (en)	1976-06-13
US3953440A (en)	1976-04-27

Publication	Publication Date	Title
JPH0313237B2 (nl)	1991-02-22
JPS6339868A (ja)	1988-02-20	ジ低級アルキルフエノ−ル誘導体
JPH0149271B2 (nl)	1989-10-24
PL80548B1 (en)	1975-08-30	METHOD OF PRODUCING 7{62 -ACYLAMIDO-3-METHYLCEPH-3-Em-4-CARBOXYLIC ACID ESTERS[US3725399A]
PL85390B1 (nl)	1976-04-30
JPH01156969A (ja)	1989-06-20	酢酸誘導体およびその塩
PL105054B1 (pl)	1979-09-29	Sposob wytwarzania estrow kwasu 7-acyloamido-3-metylo-3-cefemokarboksylowego-4
US4933469A (en)	1990-06-12	Method for preparing oxybisphthalimides
JPH06501271A (ja)	1994-02-10	セフォロスポリン中間生成物の製造方法
WO2001036383A1 (en)	2001-05-25	Process for the preparation of sulfamides
US4354022A (en)	1982-10-12	Process for preparing 3-methylenecepham compounds or a salt thereof
SU715021A3 (ru)	1980-02-05	Способ получени производных 2,1,3-тиадиазин-4-он-2,2-диоксида
JP3068143B2 (ja)	2000-07-24	アシル化法
PL101194B1 (pl)	1978-12-30	Sposob wytwarzania nowych pochodnych tiazoloizochinolin
JPS6254112B2 (nl)	1987-11-13
DE2728578A1 (de)	1978-01-12	Verfahren zur herstellung einer beta-lactamsaeure
CS236483B2 (en)	1985-05-15	Method of 5,6,7,7a-tetrahydro-4h-thieno-(3,2-c)-2-pyridinone derivatives production
JPH02117680A (ja)	1990-05-02	３―クロロセファロスポリン骨格を有する化合物
JPS585199B2 (ja)	1983-01-29	置換ペニシリン類の製造方法
US3966720A (en)	1976-06-29	Process for producing desacetoxy cephalosporanic acid compound
KR790001071B1 (ko)	1979-08-24	페니실린 설폭사이드를 전위시켜서 테아세톡시 세팔로스포린을 제조하는 방법
PL92439B1 (nl)	1977-04-30
US4244885A (en)	1981-01-13	α-Substituted-3-(halomethyl)-4-hydroxybenzeneacetic acids
CS214694B2 (en)	1982-05-28	Method of preparation of the cefalosporine solvates
Ivanov et al.	2002	New condensed heterocyclic system with a bridgehead phosphorus atom